There's no such thing as sure thing. That's why they call it gambling - O. Madison 🪪 AKA @BillSperos 🐶 Dad 💰 Paid $8
Founded 1965 - ® 2016
Joined June 2011
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Obnoxious Boston Fan retweeted
Underdog is clearly betting that product velocity + prediction markets + diversification (Rips, legal fights) will keep it among the survivors in a crowded, high-spend category while the sale and potential SCOTUS clarity play out.
@Underdog CEO @JerLevine spoke with @RotoWire for a wide-ranging interview as the company navigates a major transition:
✅️ Sale set to close in 2027
✅️ First full NFL season on prediction markets
✅️ DFS pulled back in some states
✅️ A rapid expansion into card “Rips.”
Key takeaways:
• Prediction markets are the clear priority. In September, they would have generated 40x more revenue than Drafts (DFS) in the states where both could have run. Levine called the decision to stop DFS in certain jurisdictions “very easy” on the numbers but still painful because he loves the product.
• Users in some places can trade via Aristotle Exchange, play DFS, or buy into Rips depending on location.
• Legal posture remains aggressive. Underdog has sued seven states. Levine’s view is that sports event contracts are swaps that should be federally regulated by the @CFTC. The company built its stack so it can flip states or products on/off in real time if the Supreme Court (expected 2027–28) rules the other way.
• Marketing is part guerrilla. Credit goes to the internal team he calls “The Rascals”: plane banner over Fenway calling for John Henry to fire Craig Breslow and sell the Red Sox, Lane Kiffin urinal cakes and toilet paper in Oxford, an “Unethical Hoops” board game roasting Shai Gilgeous-Alexander’s foul-drawing, and same-day LeBron billboards in Philly. Levine says he doesn’t even generate the ideas—they just surprise him.
• First NFL season on prediction markets: “great.” Fantasy only covered roughly a third of what fans want to express opinions on; prediction markets get them to “damn near 100%.” He argues the category is already mainstream—most sports fans know Kalshi, Polymarket, DraftKings, and Underdog even if they haven’t activated yet.
• On the pending sale: culture and day-to-day should stay largely the same. He knows and trusts the buyer, is staying on to run the company, and has been telling the team their jobs won’t change much. He’s already done his first public-market-style presentation.
• Super Bowl pick after a long pause: the Patriots.
Full interview: rotowire.com/article/underdo…
Obnoxious Boston Fan retweeted
John Henry is going to get his salary cap or burn 🔥 down the 2027 season trying
Opening Day +/- July 1
Congratulations Brewers!
See you in July, Baseball ⚾️
(Some of us were Brewers fans before it was trendy. 😎)
Obnoxious Boston Fan retweeted
.@DraftKings is extending its longstanding marketing relationship with the NBA into prediction markets. The agreement expands our ability to reach and engage eligible customers around NBA event contracts throughout the league ecosystem, complementing the continued expansion of DraftKings Predictions within our broader sports platform.
Obnoxious Boston Fan retweeted
This season, Sam Darnold and the Seahawks have beaten the only 2 AFC Super Bowl champions since 2016.
Obnoxious Boston Fan retweeted
Happy Sports Equinox!!!
World Series
Monday Night Football
NBA
NHL
Full Story & More
bookies.com/news/2026-sports…
Big NBA news
🚨 BREAKING: The @NBA has reached a long anticipated "Memorandum of Understanding" with federal prediction market regulators and has named @Kalshi and @Polymarket its Preferred Market Exchanges.
The NBA becomes the final major pro sports league in North American to take a stance on prediction platforms.
The deal includes:
✅ Marketing and licensing rights
✅ Official @NBA data via @Sportradar
✅ Limits on permissible markets
✅ A ban on league and team personnel trading NBA event contracts
✅ Info-sharing obligations on investigations and suspicious trading
✅ An MOU with the CFTC to support a regulated, transparent framework
Full Story & Analysis In Comments 🔽
Happy Sports Equinox Eve!
The 2026 Sports Equinox Arrives Tomorrow
See how all the planets align in the sports world, and the best ways to wager your way though it all without being lost in space.
via @Bookies
bookies.com/news/2026-sports…
This was covered in 1972 when Pauline Kael famously did not say "I don't know anyone who voted for Nixon."
Nixon won 49 states
Her actual quote
"I live in a rather special world. I only know one person who voted for Nixon. Where they are I don't know. They're outside my ken. But sometimes when I'm in a theater I can feel them."
"This is liquid insurance. Weather. Election contracts."
- Berger
This would be where the remaining capital beyond sports would come from - 70% non-sports
(via Sanford Bernstein)
"I think this is probably a similar set of issues that we've confronted for someone who's involved in sports betting a long time, and they're serious issues, but they have to be weighed against the business model and its other benefits." - @Eggernomics
"Let e make a crazy statement. People that I know in the industry think that there is a possibility. possibility that this grows bigger than the stock market." - Neal Berger Eagle View Capital
Sports
"We see a 60% probability that (the Supreme Court) affirms the CFTC's jurisdiction over prediction matkets. Which means that there's a certain sense that this is here to stay, and public equity players in the sports betting space are investing in this business."
@Eggernomics Bloomberg
Hedge Funds
"We see it growing is well beyond sports (to) liquid insurance. If I own a ski resort and I'm going to really have a bad year if it snows less than 10 inches a year, I want to protect that."
Is there enough volume beyond sports and politics:
"Not yet"
Neal Berger, Eagle View Capital
"We're at the beginning, the really very beginning of a hyper growth cycle for prerdiction markets as an asset class, both for retail but extending into what institutions want to be participating in as well."
- Jeannie Hightower-Sellitto $DKNG
"Prediction markets clean up the information ecosystem." - @chucktodd
We'll be covering @nextpredictio here . . .
(Since @elonmusk won't let me in to my other @BillSperos account)
Obnoxious Boston Fan retweeted
The CFTC ordered Novig and ProphetX not to list certain sports event contracts they've self-certified, FOS has learned.
“It’s kind of a warning shot” to prediction markets, one source says.
frontofficesports.com/articl…
We'll be covering @nextpredictio here . . .
(Since @elonmusk won't let me in to my other @BillSperos account)
Obnoxious Boston Fan retweeted
EXCLUSIVE: A new study finds that political prediction market traders are not representative of all voters, but election market prices are more accurate than leading poll-based methods and not politically biased.
The study found:
✅ In its first month of listing election contracts in 2024, Kalshi's prices beat every poll-based forecast (Silver Bulletin, FiveThirtyEight, The Economist) in the national race, all seven battleground states, and 19 Senate races
✅ A trader who believed the poll-based models and traded against Kalshi's national price would have lost 92 to 100 cents per dollar.
✅ No poll-based forecast would have been profitable to trade against Kalshi in any group of presidential contests.
💰 @Kalshi's 2024 election traders were 86% male and half were under 30.
🏠 Their home zip codes voted 28% for Trump. A market that priced its traders' politics would have leaned toward Harris, not Trump. Instead, 60% of the money went to Republican positions, and Kalshi priced Trump as the favorite through the final month.
🔢 The study used data from @Kalshi in 2024, @PredictIt in 2016, and New York betting markets from 1884 to 1940.
✍️The study was authored by @HarryDCrane, Professor of Statistics at @RutgersU and member of @CFTC Innovation Advisory Committee &
@KolemanStrumpf, Burchfield Presidential Chair of Political Economy, Department of Economics, @WakeForest University.
Story via @Rotowire Below
